Cross Australia by train

The Indian Pacific is a coast-to-coast railway journey from Perth to Sydney (or vice versa), which includes the longest stretch of straight railway track in the world. Passengers spend three nights and four days travelling 4,352km through the Avon Valley, Nullarbor Plains and Blue Mountains, via Kalgoorlie and Broken Hill, where there is time to look around the old mining city. The train also calls at Adelaide, where the journey can be broken and a week spent visiting the Barossa Valley, Murray River and Kangaroo Island. A slightly shorter but equally exciting option is the Ghan, a 2,979km trip from Darwin to Adelaide (or vice versa) via Alice Springs.• From £510 (+61 8 8213 4401, greatsouthernrail.com.au)

Cross Brazil by truck

Giant water lily pads in the Pantanal. Photograph: Theo Allofs/Corbis

Brazil may be vast, but on a 26-day overland journey you can see a huge amount of the country. Dragoman's Trans Amazon Exploratory trip from Rio de Janeiro to Cusco (or vice versa) takes in the old mining district of Minas Gerais, the Guimarães national park, the Pantanal wetlands and, crossing into south-eastern Peru, a stretch of the Amazon rainforest. Most nights are spent in campsites or camping wild, but the trip also includes three nights in a jungle lodge.• Departures on 1 and 15 October, and every month to six weeks onwards, from £553, plus a kitty contribution of £825 (+1 800 805 7680, dragoman.com)

Cross Mongolia by horse

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This horse-riding challenge crosses 200km of central Mongolia, ending at Kharkhorin, the 13th-century capital of the Mongol empire. Riders follow Genghis Khan's tracks over the Khangai mountains and across the Tseterleg and Orkhon rivers, spending around six hours a day in the saddle. The ride includes a visit to Erdene Zuu Buddhist monastery, built on the site where Khan's palace once stood. Most nights are passed in ger camps (felt-lined tents used by Mongolian nomads).• £2,098 for 12 days, including return flights from Heathrow to Ulan Bator, all meals, nine nights' camping and two nights in three-star hotels (01722 718444, discoveradventure.com)

Sail around Cape Horn

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Three tall ships on round-the-world voyages are looking for crew for the 5,400-mile leg from Auckland to the Falkland Islands. No sailing experience is necessary for the 49-day journey, which crosses the Pacific around Cape Horn to the South Atlantic. Cape Horn was once a major post on the clipper trade route, and is still notorious. New sailors will learn to take the wheel, climb rigging and man the night watch.• 29 October to 16 December, from €5,375 for 49 days' full board (020 7097 1734, anotherworldadventures.com)

Cross the Sahara by camel

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Crossing the entire Sahara is quite an undertaking, considering that it is about 9,400,000km², but it is possible to spend a couple of weeks delving deep into the desert on a camel. One trek in Tunisia starts at the village of Sabria and heads south for a fortnight, finishing near the Algerian border. You spend 12 nights camping under the stars or in a Bedouin tent, and everyone has their own camel to ride or walk beside (apparently, riding is comfortable when you get the hang of it).• Easter and autumn half-term, £1,053 for 15 days, with two nights in a four-star hotel, all meals, and return transport from Djerba (+33 687 170 458, adventure-treks.com)

Across America by car

Photograph: David Levene for the Guardian David Levene

Route 66, a 2,448-mile stretch of highway linking Chicago with Los Angeles, was decommissioned in 1985. However, it is still feasible to drive around 85% of the route, or even more with an off-road vehicle. A road trip along Route 66 gives a taste of the 1930s and Steinbeck's America, when migrants used it to head west to escape the Dust Bowl. At least two weeks is best for a leisurely trip, allowing time to divert to the Grand Canyon and Las Vegas.• Visit drivingroute66.com for more information, including maps, sights and places to stay

In July 1964, two men set off in a dinghy to sail from Scotland to Norway. Fifty years on, Bill Brockbank tells Charlie English how he and Frank Dye, 'the madman of the Atlantic', capsized four times, braved gale force winds and survived to tell the incredible tale of their 'holiday' on the high seas